Casey_WGDJ
TDPRI Member
The story I heard, is that the first one Waylon had the tooled body cover done on was a '68 Sunbust maple neck tele. That's the one with the white pickgaurd, it's also the one he used the most, and when he moved back to Arizona in '99 it's the only one he kept, so Shooter has that one now.
He had two others, with the tooled body cover. One was a '53 blackgaurd, and the other was a 1950 Broadcaster. He sold those in '99 when he sold his house, and most of his other stuff, in Nashville.
The '50 Broadcaster sold at a Christie's auction in 2009, for $98,500, and I think that is the one that Urban has, and I'm pretty sure the Country Music Hall Of Fame ended up with the '53.
"THE" Tele, known as #1, is actually a '53, not a '68. It was given to Waylon in '63 or '64 by The Waylors. It's in the possession of his family.
The Keith Urban Tele (#2) was Waylon's main backup to his #1 for many years. He would regularly swap guitars halfway through a show. He'd typically start with #1 and switch to #2.
He had a bunch of leather covered Teles. In the '70s he started using some as backups that had a similar yet noticeably different leather pattern. You can see one of these in the intro to The Dukes Of Hazzard, as well as on the late '70s RCA reissues of Waylon's pre-outlaw albums that were given new covers.
In the early '90s the Fender Custom Shop made him several replicas of his #1. The leather pattern matched #1 much more closely than the '70s guitars. He played them a bit, probably most notably on the short "Waylon and Friends" TV series, and by 1995/96 he was mostly playing the Fender Waylon Jennings Tribute Telecasters, albeit slightly modded to his specifications (weirdly, Fender didn't use the type of Scruggs tuner that he liked). #1 was brought back for his final two years of touring with the Waymore Blues Band, and during this time he used a Tribute Tele as a backup, although as he was reduced to light strumming, I doubt he ever had a need to switch guitars on stage.
Basically, though, for the vast majority of his career, Waylon played #1. If you see a Tele with a white pickguard and a "normal" looking leather pattern in his hands, it's most likely #1.
(FWIW, I actually prefer #2! I think the black pickguard makes the guitar look pretty badass!)
As a sidenote, I have a bunch of Waylon lessons on Youtube. Here's a link: Waylon Guitar Lessons
I had to use TinyURL because my Youtube username is censored here, LOL. I guess that makes me an outlaw of sorts...